


The Wingman

by Talesmaniac89



Category: Supernatural
Genre: Blushing Sam Winchester, F/M, Fluff, Fluff and Humor, Fluff without Plot, Love Confessions, Oneshot, POV Second Person, POV Third Person Limited, Romantic Fluff, Sam Winchester Fluff, Sam Winchester in Love, Tooth-Rotting Fluff, Wingman Dean Winchester, sam winchester oneshot
Language: English
Status: Completed
Published: 2020-06-12
Updated: 2020-06-12
Packaged: 2021-03-04 04:40:55
Rating: Not Rated
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,199
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24677827
Author URL: https://archiveofourown.org/users/Talesmaniac89/pseuds/Talesmaniac89
Summary: You worry about Dean Winchester as he’s trying to act like your wingman to hook you up with Sam, unaware that Sam thinks Dean’s his wingman.
Relationships: Sam Winchester/Reader, Sam Winchester/You
Comments: 4
Kudos: 36





	The Wingman

**Reader:**  
For the last few days Dean Winchester, your best friend and the older brother of your secret crush, had been acting kind of… Well, weird as hell. Since you’d moved into the bunker your best friend had always just treated you as one of the boys. Just as ready to prank you or help you out whenever you pretended a cute bartender caught your eye to hide the fact that Sam’s flirting with some other blonde and beautiful perfect 10 was breaking your heart. 

Yet, just a few days back. His whole brotherly act had twisted. Everything from little winks to secretive smirks sent your way at random times throughout the day. His very vocal appraisals of every little thing you did or wore… He wasn’t acting like the Dean you knew. 

_“(Y/N), you look good with your hair up… Doesn’t she look good with her hair up Sammy?”_

At first, you’d struggled with the awful feeling of him possibly liking you as more than just a friend. Agonising over how you could turn the hunter, who you loved like a brother, down. Feeling awful that you had to hurt him because of your unrequited feelings for the youngest Winchester. Hell, you’d spent more than one night awake trying to rehearse and rephrase the many imaginary ways you could break it to the hunter with the biggest heart you knew. 

Though you didn’t love him like that, you still loved him, and you didn’t want him to be hurt. 

But… Just as soon as the agonising fears struck you, the reality of your situation hit like a goddamn freight train. And suddenly you wanted to _be_ the one to hurt the hunter. Of course, it was a relief that your best friend still just saw you as his. Still, Dean wasn’t in love with you, which was a relief, but he _knew_ … 

He knew you loved Sam. 

How he’d figured it out you didn’t know, but you were 99.9 percent certain. Dean Winchester knew you loved his brother, and he was doing a shitty job of keeping your little secret under wraps. 

Sam had been around for every little wink. Usually leaning closer to read a piece of lore over your shoulder or scooting over so you could grab a seat on the couch next to him. For every secretive smirk, there was a matching secret storm of butterflies in your stomach as your pulse rose to dangerous levels at the younger hunter’s proximity. 

Even the comments. Every little compliment was followed by Sam’s name. Asking his brother to back up how good your hair looked, how the top you’d just pulled out of the wardrobe was ‘very flattering’ or whatever bullshit he managed to come up with. Hell, he even kept talking about how amazing Sam was, as if you didn’t already know. Probably wanting you to agree to enact some strange form of a “you complimented each other, now kiss”-moment.

Dean knew and, just like he’d done endless times at bars with random strangers, he was trying (and failing) to be your wingman. 

So, when the older hunter entered the library where Sam and you were just settling in for a late night of researching for a fellow hunter’s monster of the week, you groaned internally. Knowing you were in for another evening of silent colour commentary about secret feelings, hidden glances and raised heart beats. 

— 

**Sam:  
** Dean had been getting on Sam’s nerves for the last week. Ever since his older brother figured out how Sam felt about you, he hadn’t shut up about it whenever the two brothers were alone. But even that was tolerable next to the way he acted when you _were_ in the room. 

Dean’s way of acting like a wingman wasn’t really _subtle_. 

Every time you were in the same room as Sam, and even remotely close to him, Dean would raise his eyebrow at the youngest Winchester. Egging him on with winks and smirks as he struggled with going past just simple greetings and hidden glances. Not that the push from Dean was even going to help… 

It wasn’t as if Sam hadn’t _tried_ to tell you. Hell, he’d attempted to get the feelings across for what felt like an eternity. But every time he wanted to say anything, to tell you he loved you, the feelings he wanted to confess just came out as simple hellos, good nights and good mornings. Turning every word he spoke to you into secret confessions of love.

Meanwhile, his older brother had no problem attempting to translate Sam’s unspoken feelings into English. The older hunter would constantly compliment you whenever you walked in the room asking for Sam to back him up. 

Teasing out stuttered soliloquies that were only mere fragments of the words Sam’s mind used to describe your absolute beauty and perfection every single day. Making him cringe over his dull little “you look pretty” replies, as his mind added verses upon verses about how your (Y/E/C) eyes caught the light, how the sound of your laughter was what dreams were made of, or how much he loved the way your smile always made him feel better, brighter even on the darkest days. 

All of which was left unspoken until he was alone in his room again in the evening. Regretting every one of the day’s actions and replaying the moments in his head. Answering his ceiling instead of you with the words he _should_ have said. Words of love and beauty painting his ceiling in an invisible mural of secret feelings, dedicated to you.

Worse yet was Dean’s favourite way of acting like Sam’s wingman, and probably the most transparent. The oldest Winchester’s constant “humble bragging” about his younger brother was textbook wingman behaviour. Though you still hadn’t seemed to catch on… Thankfully. Though Sam couldn’t help to tag a worried “for now” to the end of that chain of thoughts as Dean dropped down in the seat next to you. The younger hunter cringing in anticipation of another attempt to make you turn to face him. 

Perfect you, and broken Sam… It wasn’t going to happen, and the only thing his brother was helping Sam with, was ruining what little bond he had with you. Once you realised, things would just get awkward. Maybe it would damage your carefully crafted friendship. Hell, maybe it would scare you away from the bunker forever. Maybe you’d never smile at him again. 

No matter what - this whole shitstorm could only end with heartbreak. With Sam’s heart as the unwilling sacrifice.

—

 **Reader:  
** “Hey (Y/N)?” As Dean spoke up, the innocent words made you flinch from the clearly up-to-no-good smile that followed them. 

Waiting for another forced compliment from Sam through Dean, or some other new and creative way to hint at your infatuation with the younger hunter, your hand gripped the old tome in your hands a little harder. Your eyes refocusing back on the words on the page with a noncommittal mumbled noise of acknowledgement. Waiting for whatever new dissection of your feelings would be performed on top of the library table that evening.

Though, for once, Dean surprised you by staying clear of the topic. Choosing instead to focus on the research in front of him. His refreshingly innuendo free question made your tense shoulders instantly relax. Though in the dark suspicious depths of your mind, you still clung to a thread of that wariness.

“Which of these books should I start with?” The older hunter asked, holding up two books for you to glance at out of the corner of your eye. Looking over at the two ancient books you simply nodded towards his right hand, relief clearly evident in your eyes as Dean gave you a boyish, teasing grin. Letting you know that he hadn’t missed the obvious way your body relaxed at the innocent question. 

“That one. We’re looking for info about a possible djinn subspecies to help out on a strange case in New York,” 

With a silent nod, Dean dropped the other book back onto the library table with a dull thud before hunkering down over the dusty pages of the book you’d pointed out. As his eyes scanned the page, you were rewarded with no more than a few seconds of silence before the older Winchester clearly decided to audition for the role of annoying best friend once more with an overacted sigh. 

“This one’s too much for me… Someone smarter should read it,” The hunter groaned out words that were clearly a load of bull. Dean Winchester was one of the smartest men you knew. So, this was clearly a ploy. And you could guess what was coming next. “Hey (Y/N)… Did you know? Sam’s super smart, he even went to Stanford. This book won’t be a problem for him,”

Focusing your full attention on the page in front of you, you burned the words into your eyes to keep from rolling them and rewarding Dean’s obvious ploy and poor acting. Opening your mouth to shut the hunter down you were just a second late as Sam beat you to it. 

“Shut up Dean,” The words were no more than a mumble over the top of the book the younger Winchester, and the lead actor in all of your daydreams, was reading. The exasperation those three words were soaked in was the only hint at the expression hiding behind the leather binding as Sam kept his head in the book. 

“Yeah, you’re right, we have work to do. You’ve always been the responsible one…” Dean sighed. The book forgotten on the table and his poor acting skills still very much intact even with the less than stellar reception of Act 1. “Sammy’s very responsible, isn’t he (Y/N)?”

“I know Dean… Now _please_ focus on the research,” Your own sigh was very much _not_ an act as you shot daggers at your best friend out of the corner of your eye. Ignoring the bright shiteating grin he gave you in return. As well as the cheeky wink that followed. 

“Alright, alright… We’re all serious today,” Dean said with a roll of green eyes as your own (Y/E/C) eyes burned into him. Silently promising him a world of hurt if he didn’t _calm the_ _fuck down_. 

Taking your silent threat seriously, your best friend raised his hands in a quiet surrender. The bunker easily returning to the comfortable silence of rustling paper as Dean picked the book up again. Not adding any further complaints about the complexity of it as he flipped through the pages looking for hints. 

—

The silence lasted for half an hour give or take a few minutes. 

Though it felt like no time at all had passed as the sound of Dean’s fingers tapping against the wooden table drew you out of a paragraph about Baltic genie myths that could possibly point at a subspecies. The tapping growing increasingly louder as the older hunter made no attempts at hiding how he was trying to get your attention. 

Glancing at him from out of the corner of your eye, you watched as your best friend looked from Sam to you and back again. Clearly debating something with his conscience and need for absolute mayhem as green eyes followed the well beaten path between you and your crush. 

A pat your own eyes had often taken to cast secretive glances at a certain Sam Winchester. Well, not so secretive it turned out. Since Dean had easily interpreted those glances for exactly what they were.

As the annoyed crease in his brow slowly but surely disappeared, only to be replaced with a smile, you steeled yourself. The confident smirk that replaced the internal round table discussion with the angel and devil on Dean’s shoulders instantly terrifying you. He was up to something, and whatever that something was, it _wasn’t_ good. 

The sound of his chair scraping jostled you fully out of the pages of the book as you looked up at him. From across the table you could see Sam flinch and look up at his brother from behind his book as well. Hazel eyes dark with worry as that cute confused crease that always made you feel all tingly made a guest appearance on his brow. Just slightly hidden by the hunter’s soft brown hair. Clearly Sam was seeing the same thing you were. And neither of you trusted the bright gleam in Dean’s eyes as he turned his chair to face you fully. 

“Hey… Do I know you?” He asked, the same cocky grin brightening as you looked on confused. Your mind trying, and failing, to figure out where your best friend was going with this one.

“Uhm… Yes, you do Dean…” You hesitated over the words. Unsure what would be the right thing to say to stop whatever train wreck was happening from, well, happening. 

“‘Cause you look like my future sister in law,” Dean finished with a flourish and an overacted wink. Clearly choosing to ignore your words completely as he delivered the slightly edited pickup line your way. 

“Wha…” Your mind was blank. Dean had taken his little joke too far. Looking from Dean to Sam and back down to your book, you tried to find the words you needed. But Sam beat you to it, his low rumbled voice sounding equal parts embarrassed, confused and outraged. 

“Did you just hit on (Y/N)? _For me_?” Sam’s words were barely above a whisper as he looked at his older brother. There was a quiet anger and something more, something smaller and scared, in his voice as the words trembled across the table. Reaching both you, frozen in place, and the older hunter whose grin was fading slowly when faced with his younger brother’s quiet rage. 

Yet, you missed the silent argument that was happening between the two sets of eyes belonging to your best friend and the man you loved. Your mind loud and noisy with the many different creative ways the younger hunter could voice what was basically a direct rejection of your feelings. There was, after all, no way Sam could misunderstand Dean’s words. Not when he practically spelled out your feelings in plain English. Your spiralling mind only breaking free from your early attempt at crushing your own heart before Sam could as Dean’s palms slapped against the table making you jump in your seat.

“Someone had to!” Dean shouted, but there wasn’t actual anger there. More just long pent up frustration as the words echoed across forgotten research books in the library. “I’m sick and tired of this whole will-they-won’t-they thing. I feel like I’m living in a damned chick flick! And, in case you missed the memo, I _hate_ chick flicks!”

Giving neither of you a chance to fight back or deny his words. Dean jumped fully out of his seat; one hand still anchored to the wood of the table as the other one pointed directly at you.

“(Y/N)!” Though you already knew what was coming, you couldn’t help but flinch as Dean called your name. In some twisted forced confession roll call. 

“Yeah?” Your voice broke over the one-word reply, knowing he was about to either tell Sam himself, or force you to vocalise your feelings. Yet… What followed was exactly the opposite. 

“My brother here is madly in love with you,” Dean said, his hand that had been pointing at you easily swinging across the table to point at his brother instead. Sam barely even took note of the finger pointing at him. His eyes wide and jaw dropped as the big guy was growing both pale and red simultaneously. His heart sending all the blood to his head in an act of a rebellious standoff featuring logic versus emotion. 

“Sam…” Dean continued, clearly not done just yet.

“Sam!” Dean barked, a little louder, in an attempt to pull the younger hunter out of his daze as he barely registered the roll call. His wide hazel eyes going back and forth between his brother and you in shock and what seemed to be the early stages of embarrassed relief of finally having the truth out there. 

“Sammy!” Dean’s insistent third attempt was just enough to draw a small nod out of the youngest Winchester. Which the older hunter clearly deemed as enough of a reply as he spilled the secret you’d promised yourself to never voice.

“(Y/N)’s obviously been in love with you since… Hell I don’t know, since forever,” 

As the words left your best friend like a slow-motion action scene in one of those movies he loved just a little too much, you watched as Sam’s eyes stopped moving between the two of you. Instead choosing to come to a full stop on you as his brother’s words fully sank in. 

Those warm brown eyes you loved going from worried and questioning to a cautious warm hope as you sat stunned. Left unable to move or speak through the cottonmouth that followed Dean’s impromptu stolen confession on your behalf. 

You were rooted to your seat in shock as your eyes just numbly watched Sam. Your mind reeling as you tried to get your brain to catch up to the lightning fast development orchestrated by your best friend. Dean Winchester had just ousted you to your crush. That and… 

_Wait_. 

Did he say Sam was in love with you too?

“Wha…” Sam stopped himself from even attempting to speak through the shock as his voice broke over the very first word. Clearing his throat, his warm hazel eyes instead searched yours across the table. The careful question they asked louder than your own frantic heartbeat, as you forced your body to listen to you again.

Taking a shaky breath, you gave the man you’d been in love with for yearsa shy smile. The small gesture enough to make the eyes of the man you’d spent countless days, and nights, daydreaming about brighten. His own small, hesitant smile quickly grew as the mixture of your smile and his brother’s words fully sank in. Your own smile just as easily growing to echo it as you finally fully realised it was true. 

Sam loved you too. 

The few seconds of sweet silence as you just marveled at that fact, were just as rudely interrupted by your best friend as your years of quiet pining had been. The older hunter easily brought your attention back to him from where you’d been getting lost in Sam’s eyes with a fake tired sigh. Though you couldn’t make yourself stay angry at your very own cupid in a ratty AC/DC t-shirt. 

“There! You’re both in love and you’re both welcome. Now maybe we can get some work done here huh?” Dean’s cocky smirk and fake scoff made you want to elbow him in the stomach. Yet your body was still not done catching up with you as you simply rolled your eyes at your best friend’s antics. “I guess thank yous are in order huh? To me I mean…”

“Oh, how can we ever repay you,” The sarcastic words that left Sam, underlined and punctuated by a trademark annoyed glare, beat your own by just a fraction of a second. Both of you still only glanced over at the other hunter in the room as you kept getting drawn back to each other. To marvel at the miracle that was mutual feelings. 

“You can be my wingman any time,” Dean laughed from somewhere next to you. Though you didn’t turn to look at him, as you instead focused on Sam’s annoyed reaction to the movie quote. The way his brow furrowed and how his hand went up to pinch at the bridge of his nose sending little electric shocks through you. Yeah, you were a goner, anything the younger Winchester did had your heart racing.

“Dean, this isn’t Top Gun… You better not have planned _all_ of this just so you could say that quote,” The younger Winchester shot back, eyeing his brother with slight wary suspicion. The words finally made you tear your eyes off Sam as you turned to throw an incredulous look towards your best friend. 

The older hunter answering your suspicions, not in words, but in actions. As he laughed out loud and took the words as his cue to flee the room.

“Really Dean?!” 

Your tired outrage mirrored Sam’s as you responded in unison to the quickly retreating back of one Dean Winchester. Though, where you couldn’t help but laugh, Sam was clearly sulking at his brother’s antics, which only served to squeeze at your heart a little more.

As Dean retreated and your laughter died down, the library grew silent once more. Both Sam and you unsure where to go from there. Feelings had been voiced, but not from either of you. And so, a part of you was still hesitant to act on what you knew you felt, and now were _pretty damn sure_ Sam felt too. 

Clearing your throat, you looked into Sam’s warm brown eyes again. Looking to borrow some courage from one of the bravest men you knew as you readied yourself to speak words you’d never planned on saying out loud to anything but your bedroom ceiling. 

“So…” Cursing your own cowardice you simply looked down. Trying to find the words in the palms of your hands and finding nothing but air and shaky fingers. 

From somewhere across from you, you heard the tell-tale sign of a chair pulling away from the library table and, within just a few seconds, Sam’s hand was on yours. Placing strength, feelings and a piece of his heart in your hands as he crouched by your chair, looking up at you through your curtain of (Y/H/C) hair. 

“You love me…” Sam whispered. The words were not exactly a question, yet not exactly a statement. They fell somewhere in between. Inside that little piece of magic and marvel that was softening the whole moment in cotton candy sweetness. 

“I love you,” You said, adding that final layer of truth that brought substance and sincerity to your feelings. Your voice shaking over unexplored emotions as you watched Sam’s eyes grow impossibly bright and warm. The hunter still kneeling by your chair looked as if he was finding the shape of a new religion and some form of worship in your revelation. Awe and wonder making the beautiful man look younger as his eyes crinkled from another wide smile. 

“And… You love me,” You added, still slightly hesitant as you watched Sam’s hand raise from his side to gently brush your hair out of your eyes and behind your ear. His fingers lingering against your skin and tracing the shape of your jaw, as if to convince himself you were real.

“I do. I love you,” Sam’s voice was thick with emotion as he straightened up until he was eye level with where you were sitting. His forehead bumping against yours with a wry smile as he drowned in your eyes and you his. “I guess we’re both cowards huh?” He added with a breathy chuckle. His words barely above a whisper yet reaching you easily where you rested your forehead against his. 

“Yeah…” You laughed. A careful smile building as you glanced down and took his hand in yours, painting small circles on his palm. Still not used to being that open about your feelings, you hid in the simple pattern as you confessed a little more. “But… I’m too happy to care,”

“Me too,” Sam’s sincere words were a bit louder as he moved to sit on a chair next to you, pulling your chair closer until your knees were between his. “I just can’t believe it… You love me,” He added with a marveled whisper. Looking at you like you were the most precious part of his existence. Like everything, all the _bullshit_ , pain and suffering, had been building up to this. To well-deserved happiness. 

His warm smile shifted into something more careful and slightly deeper as he slowly leaned in. Hazel eyes dipping to trace the shape of your lips and his teeth grazed his own. A big hand raised to gently trace the shape of your jaw as he softly angled your lips up towards him. Just seconds away from the kiss you’d been dreaming about since… Well, what felt like forever. 

“And, as the music swells, Sam Winchester leans in… Ready to wrap (Y/N) in his warm embrace…” Your best friend and much-loved pain in your side, Dean Winchester, was putting on his best movie trailer voice in a poor attempt at narration. Easily interrupting the sweet moment just as you could feel Sam’s warm breath like the ghost of a kiss to brush against your lips. 

Sighing, you felt Sam’s forehead drop against yours again. Both of you shared an annoyed look before you squeezed your eyes shut and called out to the man who was simultaneously the best and the worst wingman in history. 

“Dammit Dean!”


End file.
